Young, Single, and Sick of Dating: Why I Trusted a Matchmaker to Find me a Man

While typical nights after work usually involve Netflix and a quickly-made veggie burger, one recent evening I found myself in a hotel bar with a group of women I’d never met before, all vying for the attention of a matchmaker, while discussing who had resorted to freezing their eggs, plastic surgery, and what we each saw when we looked in the mirror.

Before I get into why I enlisted a professional matchmaker to find me a guy, here’s a little bit about my thoughts on dating: I’m a 23-year-old beauty editor living in New York City, and meeting someone who’s legitimately interested in a serious, accountable relationship—free of midnight “come over” texts and casual expectations—has proved difficult. Even for someone like me, who certainly doesn’t present herself as someone looking to lock down a ring or any of that.

I’ve met guys out at bars, I’ve tried the Tinder thing, and most recently I dated someone casually for six months, only to find out that he couldn’t see himself getting serious with anyone “because of work.” So … yeah.

It was after one horrifically disastrous first date with a guy I met online who got way too touchy way too soon (seriously—ick), that I happily accepted the offer to write about what it’s really like to use a high-end professional matchmaker to meet men, with a real hope that I’d not only get a good story out of it, but maybe meet a nice guy. And so began one of the strangest, most intense, and all-around emotionally consuming periods of my dating life so far.

I realize that, to some, matchmakers are considered a “last step” of sorts—the person you go to when you absolutely cannot meet someone on your own after years of trying. I honestly felt a tinge of embarrassment and uncertainty about it too, largely thanks to pop culture connotations (ahem, “Fiddler on the Roof” and Patti Stanger of “The Millionaire Matchmaker.”) But after seven solid years of dating, it’s not too hard to feel like you’ve exhausted your options.

My introduction into the matchmaking world came via Janis Spindel Serious Matchmaking, a service based in New York City run by mother-daughter duo Janis and Carly Spindel, both of whom have pretty impressive stats to boast about when it comes to getting people together. Janis, who has been in the business for 20 years, attests to having married over 1,000 couples, while her daughter Carly has 82 marriages to her name in six years.

Here’s how their service works: If you’re a guy looking to land a lady, you sign up for Carly’s help—and you can expect to pay a hefty fee ranging from $25,000 on up to $100,000. Regardless of the fee, her male clients get matched with a maximum of twelve women.

For guys, the matchmaking process starts with a “simulated date” with the matchmakers before they’re officially signed on as a client, which Carly tells me is a key differentiator between what she does and online dating. “We do background checks on our clients. We do home visits. We’ve gone on dates with them. We watch them with their manners. Are they sitting alone? Are they polite? Do they stand up when [you] go to the bathroom? How do they treat the waiter? Are they rude? What kind of tip do they leave? We’re basically judging them on everything possible that you can be judged on.”

Also of note: They say they only accept commitment-minded clients for whom they’re sure results can be delivered. That means it’s no dice for a 75-year-old man seeking a 20-year-old girlfriend, and a dude who admits he only wants a fling won’t make the cut.

For women, it’s an entirely different ballgame. The first step is filling out a rather intensive $25 application online, which includes questions about everything from your travel history to your weight, and requires you send a headshot.

The women that the Spindels accept must fit the “4 B’s” criteria, they say—beauty, brains, body, and balance. If you don’t meet those requirements, Carly tells me you’ll get an auto-generated email with some dating tips and the invitation to apply again.

Once you’re accepted, however, you’re forever in their “love sphere” meaning that if they come across a guy that could be a good match for you two years down the line, they’ll give you a call. Carly attests to having over 57,000 women in her database in more than 32 cities. “We’re very selective with who we take on as members and even more selective with who we take on as clients,” she says.

After deciding I was ready to take the plunge, I wrote my abbreviated life story for the application, picked out what I thought were my two best photos, and waited for my acceptance email. Twenty-four hours later, I was in.

Illustration: Candace Napier

The next step for women is to either meet with Carly and Janis separately (this will cost you extra cash) or attend a group “meet and greet” of sorts, an event held in a private room of a swanky hotel that costs $250 (full disclosure: that fee for me had been waived.)

It was hard for me to imagine that a mixer with a ton of other man-hunting women could possibly work to my benefit. Carly has a different take: “We love women networking. You could be sitting next to someone who says, ‘Oh my god. You’re so gorgeous. I have a son for you.’ She could be in her 50’s. We believe that every woman is a wingwoman.”

Before I got to the mixer, I’ll admit I expected to be among middle-aged women with caked-on makeup and swathed in Hervé Léger bandage dresses, gossiping over glasses of Pinot Grigio. I just assumed I’d find myself in the nexus of “Bachelor” meets “Real Housewives” universe where we’d all be competing for the same man. Well, you know what they say about assuming.

Instead, I found myself surrounded by female publishing executives, authors, hedge fund managers, and even a woman who had run for Congress. “Women come to us as members as another way of being proactive with their love life,” Carly shared. “They’re busy and they don’t have time to look for Mr. Right, so they come to us in hopes that he’s one of our clients.”

Not surprising, given the fees for her services, Carly’s male clients have equally impressive resumes. She jokes that her matchmaking service basically runs what could be Cupid’s Wall Street office, speaking to the number of investment bankers that have crossed her desk over the years. “The male clients are CEOs, politicians, attorneys, bankers, hedge fund managers, entrepreneurs. You name the industry, and I’m sure there’s a client who’s there.”

At the meet and greet that night, we talked through a variety of topics from children to careers. I eventually spilled my guts, telling the group about what a superbly shitty past relationship had taught me about what I wanted from a future partner.

But, at a certain point, the group therapy session of sorts took a bluntly instructive turn. We all learned our photos—the ones we submitted before we were accepted—weren’t doing any of us justice. And if Carly and Janis don’t like the snapshots, you don’t get introduced to anyone. Bottom line—each and every one of us was told we needed new pictures. I also learned, apparently, guys aren’t into those serious, sultry faces we make into our iPhone camera when taking a selfie, and smiles usually win with men looking for a date.

I don’t know if this reality check brought me back to the “swipe right, swipe left” complex I was so desperately trying to escape or if I was a little self-conscious about the fact that the pictures that I thought were my most attractive moments just weren’t good enough, but it was hard to not feel defensive.

At one point, I wanted to stand up and tell the chick across the room from me, “Who cares if he doesn’t like your photos? Forget him! Let’s go. We don’t need this.”

I kept my butt in my chair, though, and reminded myself that this was paid-for advice from two people trying to match happy couples. Hinge certainly doesn’t share these brutally honest suggestions.

Illustration: Candace Napier

I got to work on making those new photos happen the next day, and begged my office’s in-house photographer to snap some more flattering pictures of me (a perk of working at a media company, I know). After a few back and forths with Carly, more pleading emails from me to my colleague for more photos, an outfit change, the addition of a bold red lip and several layers of mascara, the camera caught a decent moment that was flattering but still read true to my personality.

Now that Carly had good photos, she was ready to make a match. This part of the process comes down largely to the matchmaker’s intuition, but Carly also takes into account certain demands of her paying client like religion, and any penchants for specific physical traits. If she thinks she has a match on her hands, she’ll send the client your photo along with some general information, and if they’re into you, an introduction is made. As a woman going through the process, my work from this point on is done. No more pictures, no more meetings, it’s all up to him and whether he’s feeling the potential connection.

This part of the process felt like an introduction to old school dating. If a guy is into you, he is instructed to call you to set up a date—something I’ve always considered foreign (I don’t think I’ve ever been asked out on a first date via an actual phone conversation).

And so the waiting game began. By day five, I started to get that insecure pang of “why doesn’t anyone like me?” in the pit of my stomach. The lack of control in the process was definitely starting to get to me.

And then one evening, two weeks later, and email from Carly arrived: “He went to NYU, is handsome, in good shape, loves cooking, lives in a gorgeous apartment. He’s well dressed, likes to travel, very smart, owns three businesses, and is awesome. He’s turning 31 this year. Any questions?”

I had been pre-warned that this was the extent of the information I was going to get, and that I wouldn’t be able to see what the guy looked like until the date, but I also know more personal information about my dry cleaner.

That same night that Carly’s email arrived, I got a missed call, and woke up to a lovely voicemail (I guess people do still leave those) from my match. It was really happening.

Illustration: Candace Napier

I waited until lunchtime the next day to quickly escape and give him a call back. A few rings later, he answered. He was pleasant, but the conversation lasted, all in, just one minute, with him telling me he’d call me on Sunday to make a solid plan.

That Sunday came and went, and so did Monday and Tuesday, and no call. It wasn’t until Wednesday when I looked down at my phone and saw a text from him asking me how I was and when we could meet up. So, he didn’t call when he said he was going to. Ladies, men you meet through a matchmaker apparently don’t have much better texting etiquette than the ones you meet on your own.

And the texts themselves, well, they left something to be desired—and they were rife with grammatical and spelling errors. I don’t have a crazy list of requirements, but I do want to marry someone who knows how to spell “weekend,” “weird,” and “brunch.” Just saying.

After some back and forth, we settled on brunch for the coming weekend. He picked a place close to my apartment, which was a score, because as much as I love pancakes, I don’t like to actually leave my neighborhood on the weekend if I don’t have to.

As the date approached, I carefully curated my outfit—an A-line skirt, crop top, curled hair—and went to meet my mystery man (who was so much a mystery that when I got to the restaurant, I almost mistook the host—a much older gentleman—for my match and basically had a coronary). Remember, I had no idea what my date looked like, which makes things especially difficult when you’re meeting someone for the first time.

Illustration: Candace Napier

A few minutes later, he appeared. First thoughts? He looked good. About six-feet tall, dark hair, blue eyes, well-dressed in jeans and a motorcycle jacket. Carly, A+.

During the first few minutes of meeting, we went back and forth ticking off the standard get-to-know-you questions: what do you do, where are you from, how many siblings do you have. The waiter had to come to our table three times before we were ready to order because neither of us had checked out the menu.

Over eggs benedict (him) and French toast (me), the conversation zig-zagged from business—he’s a fashion entrepreneur juggling several different companies—to why we were both sitting at the table that day. He told me “gold diggers” have been a problem, and so have women too eager to get married, and he’s looking for someone more genuine to share time and experiences with, he said.

And while I breathed a big sigh of relief that there weren’t any awkward silences, an immediate red flag was the fact that he barely asked me any questions, appearing more interested in talking about himself.

After brunch, he asked me if I wanted to join him on an errand he had to run. I didn’t have anything else to do, so I agreed, plus it involved going to Bloomingdale’s, so I was naturally curious. Luckily, he didn’t offer to buy me anything (that’s what all of my friends were curious about), but instead we browsed the men’s department where he asked me what I thought of various collared shirts, before he settled on one and bought it. I definitely didn’t expect to be shopping with him at that point, but I didn’t mind.

We ended the date, which lasted around two hours, with a hug. Later that day, I got a text asking to hang out again.

Now that I’ve lived to tell the tale, I see that a big pro of meeting people with a matchmaker is that working with Carly felt like a good girlfriend who wanted to find me someone who would be the right match for me. There was also comfort in knowing that even though my date was a totally unknown entity, someone I know personally had checked into this guy and he wasn’t a total freak (as opposed to online dating, where you really never know.)

The downsides? Clearly the hefty fees involved mean this isn’t for everybody. Also, not being able to see a photo of my date before it happened was difficult for me (and I imagine it would be for a lot of women.)

Bottom line: While I had some Disney fantasies about what being set up by a matchmaker would be like—I half-expected some former football star or finance type to come in and whisk me off my feet—the date I went on proved to be totally solid in the broader, more realistic scheme of dating, so let go of any over-the-top expectations.

So, did my matchmaker make me a match? I don’t know. First dates are tough—how much do you really know about someone after two hours and two pieces of toast? I guess that’s what the second date is for, which yes, we’re going on. I’ll let you know how it goes.